Pseudoceramides and cosmetic compositions comprising the same

ABSTRACT

The present invention relates to a pseudoceramide represented by the following formula (I) and a cosmetic composition comprising the same: 
     
       
         
         
             
             
         
       
         
         
           
             wherein Z represents —OH and Y represents —OH, 
           
         
       
    
     
       
         
         
             
             
         
       
         
         
           
              with the proviso that X is 
           
         
       
    
                         
Z represents —OH and X represents —OH,
 
                         
with the proviso that Y is
 
                         
Y represents —OH and X represents —OH,
 
                         
with the proviso that Z is
 
                         
R represents a linear or branched, saturated or unsaturated aliphatic hydrocarbon group; and when substituted, R has one or more —OH groups.

This application is the US national phase of international applicationPCT/KR02/00314 filed 26 Feb. 2002, which designated the US, the entirecontents of this application is incorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to novel pseudoceramides and cosmeticcompositions comprising the same. More particularly, the presentinvention relates to novel pseudoceramides showing excellentpermeability barrier similar to that found in natural ceramides andimproved water solubility and cosmetic compositions comprising the sameas active ingredient.

2. Description of the Related Art

The stratum corneum, which is located on the outermost side of the skin,serves a primary protection barrier from external irritation andinvasion of foreign substances and maintains the moisture in the skinthrough intercellular lipids.

The intercellular lipids comprise ceramides, cholesterol, free fattyacids and neutral lipids, etc. and it has been found that ceramides iscontained in the amount ranging from 40 to 50% and the most pivotallipids in the intercellular lipids. It has been reported that thedecrease of ceramide production caused by some genetic factors or agingis responsible for the weakening of barrier function of stratum corneum,thereby leading to adverse effects on the skin, e.g. atopic dermatitisand psoriasis (Fulmer & Kramer, J. Invest. Derm., 86:598-602(1986); andTupker R. A. et al., Acta Derm. Venereol. Stockh, 70:1-5(1990)).

Under such circumstances, many researches have focused on development ofprocess for preparing natural or synthetic ceramides with greaterefficiency and of novel pseudoceramides. The conventional process forpreparing ceramides includes extraction method (from animal, plant oryeast) and chemical synthetic method.

Naturally occurring ceramides show superior function but inferiorapplication to cosmetic compositions due to lower solubility, finallyresulting in high production cost.

Therefore, there remains a need in the art for novel synthetic ceramideswith excellent water barrier function, exhibiting improved applicabilityto cosmetic composition, which can be synthesized at relatively lowcost.

U.S. Pat. No. 5,206,020 discloses novel synthetic pseudoceramideprepared by ring opening the epoxide ring of a glycidyl ether with RNH₂to yield the corresponding secondary amine and then acylating thesecondary amine. In addition, U.S. Pat. No. 5,175,321 discloses novelpseudoceramide synthesized in such a manner that certain compoundprepared from glycidyl ether and ethanolamine is reacted with a fattyacid lower alkyl ester.

Throughout this application, various patents are reference and citationsare provided in parentheses. The disclosure of these patents in theirentities are hereby incorporated by references into this application inorder to more fully describe this invention and the state of the art towhich this invention pertains.

SUMMARY OF THE INVENTION

To be free from the shortcomings of natural and conventional syntheticceramides aforementioned, the inventors have researched to develop novelpseudoceramide. As a result, the inventors have developed novelpseudoceramide prepared in feasible manner and with lower productioncost.

Accordingly, it is an object of this invention to provide novelpseudoceramides.

It is another object of this invention to provide cosmetic compositionscomprising the novel pseudoceramides as active ingredient.

Other objects and advantages of the present invention will becomeapparent from the detailed description to follow taken in conjugationwith the appended claims.

DETAILED DESCRIPTION OF THIS INVENTION

In one aspect of this invention, there is provided a novelpseudoceramide represented by the following formula (I):

wherein Z represents —OH and Y represents —OH,

with the proviso that X is

Z represents —OH and X represents —OH,

with the proviso that Y is

Y represents —OH and X represents —OH,

with the proviso that Z is

R represents a linear or branched, saturated or unsaturated aliphatichydrocarbon group; and when substituted, R has one or more —OH groups.

The pseudoceramides of this invention can be prepared using uniquestarting materials with lower production cost, which is exemplified inExamples below. The starting materials employed for synthesizing thepseudoceramides of this invention have been provided by the inventors,which is disclosed in PCT/KR01/01838.

According to preferred embodiment of this invention, R group found informula (I) is a linear or branched, saturated or unsaturated aliphatichydrocarbon group and when substituted, it has one or more —OH groups.

The term “aliphatic hydrocarbon group” used herein refers to allhydrocarbon groups (for example, alkyl, alkenyl or alkynyl groups)except aromatic hydrocarbon.

As provided herein, the term “alkyl” is defined to be linear or branchedchain saturated aliphatic hydrocarbon group having designated carbonatoms, including methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl,nonyl, decyl, hexadecyl, eicosyl, triacontyl and tetracontyl, but notlimited to.

The term used herein “alkenyl” refers to linear or branched chainunsaturated aliphatic hydrocarbon group having designated carbon atoms,including ethenyl, propenyl, n-pentenyl, nonenyl, decenyl, hexadecenyl,eicosenyl, triacontenyl and tetraontenyl, but not limited to.

Exemplified pseudoceramide of this invention is represented by thefollowing formula (II), (III) or (IV):

wherein X′ represents H or —OH; X″ represents —OH,

Y′ represents —OH,

Y″ represents H or —OH; Z′ represents —OH,

Z″ represents H or —OH; and n is 0 or an integer of from 1 to 47.

In another aspect of this invention, there is provided a method forpreparing the pseudoceramide represented by the above formula (I), whichcomprises the steps of: (a) preparing phytandiol amine derivative of theformula (V); and

wherein each of Y and Z is OH with the proviso that X is NH₂, each of Xand Z is OH with the proviso that Y is NH₂, and each of X and Y is OHwith the proviso that Z is NH₂,

-   -   (b) preparing the pseudoceramide represented by the above        formula (I) by reacting the phytandiol amine derivative of the        formula (V) with aliphatic hydrocarbon compound.

In the process of this invention, the step of preparing phytandiol aminederivative is exemplified in Examples and PCT/KR01/01838.

The second step of the present method is one to form amide bond, whichis exemplified in Examples, and can be carried out according to avariety of methods. For example, in the case of using carboxylic acidcompound, the carboxylic group of the compound is primarily activatedwith p-toluenesulfonylchloride or benzenesulfonylchloride (generally, inthe presence of basic catalyst, e.g., triethylamine) and the resultantis reacted with the phytandiol amine derivative of the formula (V) togenerate amide bond, thereby obtaining the pseudoceramide of the presentinvention.

Alternatively, the lactone compound can be employed in place of thecarboxylic acid compound.

In still another aspect of this invention, there is provided a cosmeticcomposition for skin care comprising (a) the pseudoceramide of thisinvention as active ingredient; and (b) a cosmetically acceptablecarrier.

In the present composition, it is general that the pseudoceramide ispresent in an amount of 0.0001-10.0 wt % based on the total weight ofthe composition. The preferred amount of the pseudoceramide is0.0005-10.0 wt % and more preferably, 0.005-10 wt %. If the amount isless than 0.0001 wt %, a moisturizing maintenance effect may benegligible; and in the case of exceeding 10 wt %, the increase ofmoisturizing maintenance effect in parallel with the increase of amountmay be rarely represented.

The cosmetic compositions of this invention may be formulated in a widevariety of forms, for example, including a solution, a suspension, anemulsion, a paste, an ointment, a gel, a cream, a lotion, a powder, asoap, a surfactant-containing cleanser, an oil, a powder foundation, anemulsion foundation, a wax foundation and a spray.

The cosmetically acceptable carrier contained in the present cosmeticcomposition, may be varied depending on the type of the formulation. Forexample, the formulation of ointment, pastes, creams or gels maycomprise animal and vegetable fats, waxes, paraffins, starch,tragacanth, cellulose derivatives, polyethylene glycols, silicones,bentonites, silica, talc, zinc oxide or mixtures of these substances. Inthe formulation of powder or spray, it may comprise lactose, talc,silica, aluminum hydroxide, calcium silicate, polyamide powder andmixtures of these substances. Spray may additionally comprise thecustomary propellants, for example, chlorofluorohydrocarbons,propane/butane or dimethyl ether.

The formulation of solution and emulsion may comprise solvent,solubilizer and emulsifier, for example water, ethanol, isopropanol,ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate,propylene glycol, 1,3-butylglycol, oils, in particular cottonseed oil,groundnut oil, maize germ oil, olive oil, castor oil and sesame seedoil, glycerol fatty esters, polyethylene glycol and fatty acid esters ofsorbitan or mixtures of these substances. The formulation of suspensionmay comprise liquid diluents, for example water, ethanol or propyleneglycol, suspending agents, for example ethoxylated isosteary alcohols,polyoxyethylene sorbitol esters and poly oxyethylene sorbitan esters,micocrystalline cellulose, aluminum metahydroxide, bentonite, agar andtragacanth or mixtures of these substances.

The formulation of soap may comprise alkali metal salts of fatty acids,salts of fatty acid hemiesters, fatty acid protein hydrolyzates,isethionates, lanolin, fatty alcohol, vegetable oil, glycerol, sugars ormixtures of these substances.

Furthermore, the cosmetic compositions of this invention, may containauxiliaries as well as carrier. The non-limiting examples of auxiliariesinclude preservatives, antioxidants, stabilizers, solubilizers,vitamins, colorants, odor improvers or mixtures of these substances

The compositions of this invention are significantly effective inenhancing moisturizing maintenance capacity of skin resulting from thepseudoceramide prepared in this invention, thereby treating, alleviatingand preventing atopic dermatitis and psoriasis.

The following specific examples are intended to be illustrative of theinvention and should not be construed as limiting the scope of theinvention as defined by appended claims.

EXAMPLE Example I Preparation of Phytandiol Amine Derivative [I]

In a reactor 0.3 g of phytantriol (0.91 mmol, Sigma-Aldrich) wasdissolved in 20 ml of normal hexane and stirred for 10 min. at a roomtemperature, followed by addition of 0.21 g (1.09 mmol) of para-toluenesulfonylchloride (Sigma-Aldrich). Following the drop of the temperatureof the reactor to 0° C., 0.11 g (1.09 mmol) of triethyl amine and acatalytic amount of pyridine were added dropwise and the temperature ofthe reactor was elevated to a room temperature, followed by stirring for12 hr. Upon the completion of the reaction, the solvent was removed bydistillation under reduced pressure. Then, 20 ml of chloroform was addedto the concentrate for extraction and the extract was washed withsaline. The washed extract was dried over anhydrous magnesium sulfate,followed by filtration and concentration to yield 0.48 g para-toluenesulfonyl phytandiol derivative as brown oil.

The yielded phytandiol derivative (0.48 g) was dissolved in 25 ml ofdimethyl formamide and 0.06 g (1.00 mmol) of sodium azide(Sigma-Aldrich) was added, followed by reflux for 5 hr in order tosubstitute azide for para-toluene sulfonyl group. The reaction mixturewas extracted with 50 ml of methylene chloride solution and washed withsaline. Following drying over anhydrous magnesium sulfate, filtrationand concentration, 0.29 g of azido phytandiol derivative was yielded.

In order to convert the azido phytandiol derivative to amine compound,0.29 g of the yielded azido phytandiol (8.4 mmol) was subject tohydrogenation in ethyl alcohol with a catalytic amount of 10% palladiumcharcoal under 50 psi of hydrogen atmosphere for 3-4 hr, and finally0.21 g of phytandiol amine derivative [I] (0.64 mmol) was obtained inthe form of yellow gel in the overall yield of 70%: Anal. Calcd. forC₂₀H₄₃NO₂ (329.33): C, 72.89; H, 13.15; N, 4.25; O, 9.71; Found C,72.63; H, 13.42; N, 4.13; O, 9.55.

The reactions in this Example is schematically illustrated as follows:

Example II Preparation of Phytandiol Amine Derivative [II]

In a reactor 0.3 g of phytol (1.0 mmol, Sigma-Aldrich) was dissolved in30 ml of methylene chloride and then the temperature of the reactor wasdecreased to 0° C. While maintaining the temperature of the reactor, tothe mixture was added 0.45 g of 77% chloroperoxy benzoic acid(Sigma-Aldrich). After the completion of the reaction, the resultant wasextracted with 50 ml of chloroform to prepare phytol derivativeepoxidated at 2- and 3-positions. The phytol derivative was reacted withammonia gas for 5 hr. to produce 0.21 g of phytandiol amine derivative[II] in the yield of 64%: Anal. Calcd. for C₂₀H₄₃NO₂ (329.33): C, 72.89;H, 13.15; N, 4.25; O, 9.71; Found C, 72.44; H, 13.51; N, 4.65; O, 9.98.

The reactions in this Example is schematically illustrated as follows:

Example III Preparation of Phytandiol Amine Derivative [III]

One g of phytantriol (3.0 mmol, Sigma-Aldrich) was refluxed usingdeanstock apparatus for 15 hr in 25 ml of acetone solution with toluenesulfonic acid as catalyst. After the completion of the reaction, theacetone solvent was removed under reduced pressure and the resultant wasextracted with chloroform solution. The extract was washed withsaturated sodium bicarbonate solution and was again washed with salineto obtain 0.3 g of(2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6,10,14-trimethyl-pentadecan-2-ol)of which 1- and 2-positions were protected.

Thereafter, in 20 ml of normal hexane was dissolved 0.3 g of(2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6,10,14-trimethyl-pentadecan-2-ol),and stirred for 10 min. at a room temperature, followed by addition of0.18 g (0.97 mmol) of para-toluene sulfonylchloride. After the drop ofthe temperature of the reactor to 0° C., 3 equivalents of pyridine wereadded and the temperature of the reactor was elevated to a roomtemperature, followed by stirring for 12 hr. Upon the completion of thereaction, the solvent was removed by distillation under reducedpressure. Then, 20 ml of chloroform was added to the concentrate forextraction and the extract was washed with saline. The washed extractwas dried over anhydrous magnesium sulfate, followed by filtration andconcentration to yield 0.41 g of a compound substituted at 3-positionwith toluene sulfonyl in the form of yellow oil. In 20 ml of 2N HCl wasdissolved 0.41 g of the yellow oil, and then was reacted for 6 hr at 80°C. to yield 0.21 g of 1,2-phytandiol derivative of which ring structureis cleaved.

The phytandiol derivative yielded (0.21 g) was dissolved in 25 ml ofdimethyl formamide and 0.06 g (1.00 mmol) of sodium azide was added,followed by reflux for 5 hr to produce 0.15 g of phytandiol derivativesubstituted with azide. In order to reduce the azide-substitutedphytandiol derivative to amine compound, 0.15 g of the azido phytandiolyielded was subject to hydrogenation in ethyl alcohol with a catalyticamount of 10%; palladium charcoal under 50 psi of hydrogen atmospherefor 3-4 hr, and finally 0.20 g of phytandiol amine derivative [III] wasobtained in the yield of 60%: Anal. Calcd. for C₂₀H₄₃NO₂ (329.33): C,72.89; H, 13.15; N, 4.25; O, 9.71; Found C, 72.51; H, 13.04; N, 4.54; O,9.43.

The reactions in this Example is schematically illustrated as follows:

Example IV Preparation of Novel Pseudoceramide 4

To synthesize pseudoceramide derivative of this invention usingphytandiol amine derivative I prepared in Example I, 100 ml of anhydrouschloroform and stearic acid (36.3 mmol) were mixed in a reactor andagitated at room temperature until stearic acid was completelydissolved. After the completion of dissolution,p-toluenesulfonylchloride (36.3 mmol) was added and agitated for 5 min.,followed by adding dropwise triethylamine as base (36.3 mmol). Upon theaddition of triethylamine, the resultant was agitated for 30 min at roomtemperature.

Then, phytandiol amine derivative I (30.2 mmol) was dissolved in 10 mlof chloroform and the solution yielded was added to the resultant,followed by allowing for reaction at room temperature. The reaction wastracked with TLC (thin layer chromatography) in order to determine thecompletion of reaction. Following the completion of the reaction, thereaction mixture was washed with distilled water (150 ml×3) and thensaline (150 ml). Washed organic layer was subject to the distillationunder reduced pressure, and to the concentrated residue obtained thus,50 ml of absolute acetone were added, followed by recrystallization at0° C. The resultant was filtered through Whatman Paper No. 5 and driedto yield 12.5 g of pseudoceramide 4 (octadecanoic acid(2,3-dihydroxy-3,7,11,15-tetramethyl-hexadecyl)amide) in the form ofwhite solid in the overall yield of 69.5%: m.p. 47-48° C.; IR (cm⁻¹)3430, 2950, 2600, 2500, 1700, 1480; Anal. Caclc. For C₃₈H₇₇NO₃ (595.59):C, 76.58; H, 13.02; N, 2.35; O, 8.05; found C, 76.51; H, 13.04; N, 2.54;O, 8.43.

The reactions in this Example are schematically illustrated as follows:

Example V Preparation of Novel Pseudoceramide 5

According to the method described in M. Merritt. et al. JACS.,120:8494-8501(1998), the hydroxyl group at the position of 2 wassubstituted with sulfate group. To a reactor containing 0.34 mmol ofpseudoceramide 4 in 20 ml of chloroform, 1.02 mmol of sulfur trioxidepyridine complex were added and agitated for 14 hr at room temperature.The reaction progress was tracked with TLC and then 20 ml of chloroformwere added to terminate the reaction following the completion ofreaction. Thereafter, the resultant was cooled to −10° C. and filtered.The yielded residue was concentrated and then recrystallized in acetonesolution, thereby obtaining 0.18 g of pseudoceramide 5 (octadecanoicacid(2-sulfate,3-hydroxy-3,7,11,15-tetramethylhexadecyl)amide) in theoverall yield of 79%: Anal. Caclc. For C₃₈H₇₇NO₆S (675.55): C, 67.51; H,11.48; N, 2.07; O, 14.20; S, 4.74; found C, 67.03; H, 11.87; N, 2.43; O,14.34; S, 4.67.

The reactions in this Example are schematically illustrated as follows:

Example VI Preparation of Novel Pseudoceramide 6

To 100 ml of anhydrous chloroform contained a reaction, oleic acid (36.3mmol) was added and agitated at room temperature until the oleic acidwas completely dissolved. After the completion of dissolution,p-toluenesulfonylchloride (36.3 mmol) was added and agitated for 5 min.,followed by adding dropwise triethylamine as base (36.3 mmol). Upon theaddition of triethylamine, the resultant was agitated for 30 min at roomtemperature.

Then, phytandiol amine derivative I (30.2 mmol) was dissolved in 10 mlof chloroform and the solution yielded was added to the resultant,followed by allowing for reaction at room temperature. The reaction wastracked with TLC and then the completion of reaction was determined.Following the completion of the reaction, the reaction mixture waswashed with distilled water (150 ml). Washed organic layer was subjectto the distillation under reduced pressure, and to the concentratedresidue obtained thus, 50 ml of absolute acetone were added, followed byrecrystallization at 0° C. The resultant was filtered through WhatmanPaper No. 5 and dried to yield 1.10 g of pseudoceramide 6(Octadec-9-enoic acid[1-(1′2′-dihydroxy-ethyl)-1,5,9,13-tetramethyl-tetradecyl]-amide) in theform of white solid in the overall yield of 61.5%: Anal. Caclc. ForC₃₇H₇₃NO₃ (579.56):C, 76.62; H, 12.69; N, 2.42; O, 8.28; found C, 76.51;H, 13.01; N, 2.63; O, 8.51.

The reactions in this Example are schematically illustrated as follows:

Example VII Preparation of Novel Pseudoceramide 7

The pseudoceramide 6 (1.0 mmol) obtained in Example VI was dissolved in20 ml of methylene chloride solution. To the resulting solution, acatalytic amount of DCC (1,3-dicyclohexylcarbodiimide, 1.2 mmol) andDMAP (4-Dimethylaminopyridine) were added and then agitated for 10 min.Phosphoric acid (2.5 mmol) was added to the reaction mixture and thenagitated for 4 hr, after which the reaction was terminated with KHCO₃.

Following the completion of the reaction, the resultant was washed withdistilled water (150 ml×3) and then saline (150 ml). Washed organiclayer was subject to the distillation under reduced pressure, and to theconcentrated residue obtained thus, 50 ml of absolute acetone wereadded, followed by recrystallization at 0° C. The resultant was filteredthrough Whatman Paper No. 5 and dried to yield 0.40 g of pseudoceramide6 (Octadec-9-enoic acid[1-(1-hydroxy-2-phosphate-ethyl-1,5,9,13-tetradecyl)-amide) in the formof white solid in the overall yield of 60.9%: Anal. Caclc. ForC₃₆H₇₁NO₃P (579.56) :C, 67.04; H, 11.10; N, 2.17; O, 14.88; P, 4.80;found C, 67.51; H, 11.01; N, 2.53; O, 14.51; P, 4.56.

The reactions in this Example are schematically illustrated as follows:

FORMULATION EXAMPLE

The following exemplified compositions were formulated according toconventional methods, which comprise the pseudoceramide 4 of thisinvention as active ingredient while the formulated compositions can bealso applied to other pseudoceramide derivatives of this invention.Therefore, those skilled in the art will promptly recognize appropriatevariations from the formulations both as to ingredients and as to theamount thereof.

Formulation I

Formulation I comprising the pseudoceramide 4 was prepared in the formof soft cosmetic liquid (skin lotion), of which composition is found inTable 1.

TABLE 1 Ingredients Amount (wt %) Pseudoceramide 4 0.5 1,3-butyleneglycol 5.2 Oleyl alcohol 1.5 Ethanol 3.2 Polysorbate 20 3.2Benzophenone-9 2.0 Carboxylvinyl polymer 1.0 Glycerine 3.5 Tween 60 1.2Perfume Minute quantity Preservative Minute quantity Distilled water To100

Formulation II

Formulation II comprising the pseudoceramide 4 was prepared in the formof milk lotion, of which composition is found in Table 2.

TABLE 2 Ingredients Amount (wt %) Pseudoceramide 4 0.6 Glycerine 5.1Propylene glycol 4.2 Tocopheryl acetate 3.0 Liquid paraffin 4.6 Stearicacid 1.0 Squalene 3.1 1,3-butylene glycol 2.5 Polysorbate 60 1.6 Sepigel305 1.6 Lipoid 0.6 Waglinol 31918 1.5 Perfume Minute quantityPreservative Minute quantity Distilled water To 100

Formulation III

Formulation III comprising the pseudoceramide 4 was prepared in the formof nutrient cosmetic cream, of which composition is found in Table 3.

TABLE 3 Ingredients Amount (wt %) Pseudoceramide 4 1.0 Glycerine 4.0Vaseline 3.5 Triethanol amine 2.1 Liquid paraffin 5.3 Squalene 3.0 Wax2.6 Tocophery acetate 5.4 Polysorbate 60 3.2 Carboxyvinyl polymer 1.0Sorbitan sesquinoleate 3.1 Perfume Minute quantity Preservative Minutequantity Distilled water To 100

Formulation IV

Formulation IV comprising the pseudoceramide 4 was prepared in the formof pack, of which composition is found in Table 4.

TABLE 4 Ingredients Amount (wt %) Pseudoceramide 4 1.0 Ethyl alcohol 3.0EDTA-2Na 0.02 Propylene glycol 5.1 Glycerine 4.5 Carbopol 1.0 Polyoxide0.1 Perfume Minute quantity Preservative Minute quantity Distilled waterTo 100

Comparative Formulation I

Comparative formulation I without the pseudoceramide 4 was prepared inthe form of milk lotion, of which composition is found in Table 5.

TABLE 5 Ingredients Amount (wt %) Pseudoceramide 4 — Glycerine 5.1Propylene glycol 4.2 Tocopheryl acetate 3.0 Liquid paraffin 4.6 Stearicacid 1.0 Squalene 3.1 1,3-butylene glycol 2.5 Polysorbate 60 1.6 Sepigel305 1.6 Lipoid 0.6 Waglinol 31918 1.5 Perfume Minute quantityPreservative Minute quantity Distilled water To 100

Comparative Formulation II

Comparative formulation II without the pseudoceramide 4 was prepared inthe form of nutrient cosmetic cream, of which composition is found inTable 6.

TABLE 6 Ingredients Amount (wt %) Pseudoceramide 4 — Glycerine 4.0Vaseline 3.5 Triethanol amine 2.1 Liquid paraffin 5.3 Squalene 3.0 Wax2.6 Tocophery acetate 5.4 Polysorbate 60 3.2 Carboxyvinyl polymer 1.0Sorbitan sesquinoleate 3.1 Perfume Minute quantity Preservative Minutequantity Distilled water To 100

Experimental Example I Evaluation on Moisturizing Maintenance Effect

Moisturizing maintenance effect of formulations II and III andcomparative formulations I and II was tested as follows:

I-1: Examination of Moisture-Retaining Capacity

In a constant temperature and humidity room at a temperature of 22° C.under relative humidity of 45%, each of cosmetic compositions indicatedabove (0.03 g/16 cm′) was topically applied to the inward region of theforearm of 30 persons and then well scrubbed. Water content of the skintreated was measured prior to application and 1 hr and 2 hr afterapplication. The measurement apparatus employed is corneometer CM820(Conrage+Khazaka), measuring the electric capacity of skin varieddepending on water content.

TABLE 7 Electrical conductivity Form. II Form. III Com. Form. I Com.Form. II Prior to 50 50 50 50 application 1 hr after 105 113 76 77application 2 hr after 86 90 60 63 application

As demonstrated in Table 7, the cosmetic compositions comprising thepseudoceramide of this invention exhibit excellent moisture-retainingcapacity as compared to the cosmetic compositions without thepseudoceramide.

I-2: Measurement of Transdermal Water Loss

By means of tape stripping on humeral region of the forearm, theprotective barrier of skin was damaged. Thereafter, in a constanttemperature and humidity room at a temperature of 22° C. under relativehumidity of 45%, each of cosmetic compositions indicated above (0.03g/16 cm′) was topically applied to the inward region of the forearm of30 persons and then well scrubbed. The amount of transdermal water losswas measured every 8 hours with TEWL meter (Koln-Germany). Therespective measurement was performed 5 times at an interval of 5 min andthe mean value was calculated.

TABLE 8 Time after Amount of Transdermal Water Loss application Form. IIForm. III Com. Form. I Com. Form. II  0 hr 4.0% 4.0% 4.0% 4.0%  8 hr−9.3% −9.9% −5.7% −5.2% 16 hr −7.6% −8.1% −0.5% 0.4% 24 hr −5.9% −6.0%3.6% 4.0% 36 hr −3.1% −3.9% 4.0% 4.0%

As indicated in Table 8, the cosmetic compositons comprising thepseudoceramide of this invention show significantly lower transdermalwater loss as compared to the cosmetic compositions without thepseudoceramide.

Having described a preferred embodiment of the present invention, it isto be understood that variants and modifications thereof falling withinthe spirit of the invention may become apparent to those skilled in thisart, and the scope of this invention is to be determined by appendedclaims and their equivalents.

1. A pseudoceramide represented by the following formula (II):

wherein X′ represents H or —OH; X″ represents —OH,

 and n is 0 or an integer of from 1 to
 47. 2. A cosmetic composition forskin care comprising (a) the pseudoceramide according to claim 1 asactive ingredient; and (b) a cosmetically acceptable carrier.
 3. Thecosmetic composition according to claim 2, wherein the pseudoceramide ispresent in an amount of 0.0001-10.0 wt % based on the total weight ofthe composition.
 4. The composition according to claim 2, wherein thecosmetic composition is effective in enhancing moisture-retainingproperty of skin.
 5. The composition according to claim 4, wherein thecosmetic composition is in the form of one selected from the groupconsisting of a solution, a suspension, an emulsion, a paste, anointment, a gel, a cream, a lotion, a powder, a soap, asurfactant-containing cleanser, an oil, a powder foundation, an emulsionfoundation, a wax foundation and a spray.